New Class of Anionic Cascade Reactions for Organic Synthesis

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The Chemical Synthesis Program of the NSF Chemistry Division supports the research of Professor Jon T. Njardarson in the Department of Chemistry and Biochemistry at the University of Arizona. Heterocyclic compounds are one of the more important structural scaffolds found in pharmaceuticals while also playing key roles in numerous other material applications. Professor Njardarson and his students develop useful new cascade reactions to make pharmaceuticals. For each one of these new cascade reactions, two simple and readily accessible building blocks are brought together in such a way that valuable complex chiral products result. In addition, this project provides excellent training of undergraduate and graduate students. Particularly noteworthy deliverables, which the students associated with these projects are involved in, are unique freely accessible educational/research tools such as pedagogical tools for structure elucidation, the free mobile app/website Chemistry By Design and, novel pharmaceutical structure analyses. The new heterocyclic methods developed in this award provide researchers in the pharmaceutical industry with new and complementary approaches for building important structures. Through the use of cascade reactions, the researchers make innovative contributions to the asymmetric syntheses of valuable heterocyclic ring structures while establishing new knowledge in the areas of a) anionic isomerizations, b) anion accelerated rearrangements, c) ring expansion reactions, d) strain assisted rearrangements, and e) asymmetric dipolar cycloaddition reactions. The many reactions emerging from this research program open the door for researchers in academia and industry to develop useful new blueprints for their target oriented synthesis pursuits. These new classes of reactions, which employ bi-functional nucleophiles, promise to be of broad scope and highly tunable. Particular focus is on elucidating and understanding the reaction mechanisms so that the resulting knowledge foundation can aid in designing new reactions and opening new avenues of investigation. These new educational products provide students, researchers and the public with new opportunities to learn about organic chemistry and its importance to society.